The Photochemical Activity of a Halogen-Bonded Complex Enables the Microfluidic Light-Driven Alkylation of Phenols

[Image: see text] A mild light-driven protocol for the direct alkylation of phenols is reported. The process is driven by the photochemical activity of a halogen-bonded complex formed upon complexation of the in situ generated electron-rich phenolate anion with the α-iodosulfone. The reaction procee...

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Autores principales: Cuadros, Sara, Rosso, Cristian, Barison, Giorgia, Costa, Paolo, Kurbasic, Marina, Bonchio, Marcella, Prato, Maurizio, Filippini, Giacomo, Dell’Amico, Luca
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9062880/
https://www.ncbi.nlm.nih.gov/pubmed/35437017
http://dx.doi.org/10.1021/acs.orglett.2c00604
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author Cuadros, Sara
Rosso, Cristian
Barison, Giorgia
Costa, Paolo
Kurbasic, Marina
Bonchio, Marcella
Prato, Maurizio
Filippini, Giacomo
Dell’Amico, Luca
author_facet Cuadros, Sara
Rosso, Cristian
Barison, Giorgia
Costa, Paolo
Kurbasic, Marina
Bonchio, Marcella
Prato, Maurizio
Filippini, Giacomo
Dell’Amico, Luca
author_sort Cuadros, Sara
collection PubMed
description [Image: see text] A mild light-driven protocol for the direct alkylation of phenols is reported. The process is driven by the photochemical activity of a halogen-bonded complex formed upon complexation of the in situ generated electron-rich phenolate anion with the α-iodosulfone. The reaction proceeds rapidly (10 min) under microfluidic conditions, delivering a wide variety of ortho-alkylated products (27 examples, up to 97% yield, >20:1 regioselectivity, on a gram scale), including densely functionalized bioactive phenol derivatives
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spelling pubmed-90628802022-05-03 The Photochemical Activity of a Halogen-Bonded Complex Enables the Microfluidic Light-Driven Alkylation of Phenols Cuadros, Sara Rosso, Cristian Barison, Giorgia Costa, Paolo Kurbasic, Marina Bonchio, Marcella Prato, Maurizio Filippini, Giacomo Dell’Amico, Luca Org Lett [Image: see text] A mild light-driven protocol for the direct alkylation of phenols is reported. The process is driven by the photochemical activity of a halogen-bonded complex formed upon complexation of the in situ generated electron-rich phenolate anion with the α-iodosulfone. The reaction proceeds rapidly (10 min) under microfluidic conditions, delivering a wide variety of ortho-alkylated products (27 examples, up to 97% yield, >20:1 regioselectivity, on a gram scale), including densely functionalized bioactive phenol derivatives American Chemical Society 2022-04-19 2022-04-29 /pmc/articles/PMC9062880/ /pubmed/35437017 http://dx.doi.org/10.1021/acs.orglett.2c00604 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Cuadros, Sara
Rosso, Cristian
Barison, Giorgia
Costa, Paolo
Kurbasic, Marina
Bonchio, Marcella
Prato, Maurizio
Filippini, Giacomo
Dell’Amico, Luca
The Photochemical Activity of a Halogen-Bonded Complex Enables the Microfluidic Light-Driven Alkylation of Phenols
title The Photochemical Activity of a Halogen-Bonded Complex Enables the Microfluidic Light-Driven Alkylation of Phenols
title_full The Photochemical Activity of a Halogen-Bonded Complex Enables the Microfluidic Light-Driven Alkylation of Phenols
title_fullStr The Photochemical Activity of a Halogen-Bonded Complex Enables the Microfluidic Light-Driven Alkylation of Phenols
title_full_unstemmed The Photochemical Activity of a Halogen-Bonded Complex Enables the Microfluidic Light-Driven Alkylation of Phenols
title_short The Photochemical Activity of a Halogen-Bonded Complex Enables the Microfluidic Light-Driven Alkylation of Phenols
title_sort photochemical activity of a halogen-bonded complex enables the microfluidic light-driven alkylation of phenols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9062880/
https://www.ncbi.nlm.nih.gov/pubmed/35437017
http://dx.doi.org/10.1021/acs.orglett.2c00604
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